Henryism as a construct draws comparisons to what is commonly referred to as respectability politics, or the active adoption of standards rooted in whiteness as a regulatory instrument of one's behavior and emotions. This manuscript will bring Henryism and respectability politics into conversation in an effort to illuminate the paradox of achievement for Black educators and professionals. By examining the experiences of Black women in higher education wrestling with racial battle fatigue, I uncover the essence and possibilities of what E. Frances White calls the 'double-edged nature of the politics of respectability', recognizable as "organized anxiety," a discourse of resistance and simultaneously an investment in stereotypes about Black people.